DBCO – VectorLabs

Bis-dPEG®₁₁-DBCO

Vector Laboratories R&D — Sat, 24 Feb 2024 02:16:47 +0000

Description
Specifications
Documents
References

Description

Bis-dPEG®11-DBCO, product number QBD-11372, is a homobifunctional click chemistry crosslinker consisting of two dibenzylcyclooctyne (DBCO) groups separated by a medium-length (39 atoms, 44.2 Å), single molecular weight, discrete polyethylene glycol (dPEG®) spacer. The DBCO groups react with azide groups via the bioorthogonal click chemistry reaction known as strain-promoted azide-alkyne cycloaddition (SPAAC), also known as copper-free click chemistry. This product is particularly useful for click chemistry reactions where the presence or use of copper(I) [Cu(I)] is undesirable. Any two molecules containing accessible azide groups can be crosslinked with this compound. Applications for Bis-dPEG®11-DBCO include crosslinking biomolecules that have been modified to include azide groups and construction of complex supramolecular structures.

Specifications

Unit Size	25 mg, 100 mg, 500 mg
Molecular Weight	1147.35; single compound
Chemical formula	C₆₄H₈₂N₄O₁₅
CAS	N/A
Purity	> 98%
Spacers	dPEG® Spacer is 39 atoms and 44.2 Å
Shipping	Ambient
Typical solubility properties (for additional information contact Customer Support)	Methylene Chloride, Methanol, DMAC, DMF, or DMSO
Storage and handling	-20°C; Always let come to room temperature before opening; be careful to limit exposure to moisture and restore under an inert atmosphere; stock solutions can be prepared with dry solvent and kept for several days (freeze when not in use). dPEG® pegylation compounds are generally hygroscopic and should be treated as such. This will be less noticeable with liquids, but the solids will become tacky and difficult to manipulate, if care is not taken to minimize air exposure.

Documents

References

Greg T. Hermanson, Bioconjugate Techniques, 2nd Edition, Elsevier Inc., Burlington, MA 01803, April, 2008 (ISBN-13: 978-0-12-370501-3; ISBN-10: 0-12-370501-0). Specifically see pp. 726-729 in his Chapter 18 on discrete PEG compounds for pegylation applications.

Greg T. Hermanson, Bioconjugate Techniques, 3rd Edition, Elsevier, Waltham, MA 02451, 2013, ISBN 978-0-12-382239-0; See chapter 18, Discrete PEG Reagents, pp.787-821, for a full overview of the dPEG® products.

The post Bis-dPEG®₁₁-DBCO appeared first on VectorLabs.

Bromoacetamido-dPEG®₂₄-amido-DBCO

Vector Laboratories R&D — Sat, 24 Feb 2024 02:16:32 +0000

Description
Specifications
Documents
References

Description

Bromoacetamido-dPEG®24-amido-DBCO, product number QBD-11224, combines a thiol-reactive bromoacetyl group with dibenzylcyclooctyne (DBCO, also known as DIBAC), a copper-free click chemistry reactive group. The two reactive groups link via a long (76 atoms, 90.0 Å), flexible, single molecular weight, discrete polyethylene glycol (dPEG®) linker. The bromoacetyl group reacts chemoselectively with thiols at pH ≥ 8.0. This differs from the maleimide group, which reacts chemoselectively with sulfhydryls within the range of pH 6.5 – 7.5. The DBCO moiety is a strained cyclooctyne ring flanked by two benzyl rings on either side. DBCO was designed for strain promoted azide-alkyne cycloaddition (SPAAC), also known as copper-free click chemistry.

Specifications

Unit Size	25 mg, 100 mg, 500 mg
Molecular Weight	1525.60; single compound
Chemical formula	C₇₁H₁₁₈BrN₃O₂₇
CAS	N/A
Purity	> 98%
Spacers	dPEG® Spacer is 76 atoms and 90.0 Å
Shipping	Ambient
Typical solubility properties (for additional information contact Customer Support)	Methylene Chloride, Methanol, DMAC, DMSO or water.
Storage and handling	-20°C; Always let come to room temperature before opening; be careful to limit exposure to moisture and restore under an inert atmosphere; stock solutions can be prepared with dry solvent and kept for several days (freeze when not in use). dPEG® pegylation compounds are generally hygroscopic and should be treated as such. This will be less noticeable with liquids, but the solids will become tacky and difficult to manipulate, if care is not taken to minimize air exposure.

Documents

References

The post Bromoacetamido-dPEG®₂₄-amido-DBCO appeared first on VectorLabs.

Bromoacetamido-dPEG®₁₂-amido-DBCO

Vector Laboratories R&D — Sat, 24 Feb 2024 02:16:29 +0000

Description
Specifications
Documents
References

Description

Bromoacetamido-dPEG®12-amido-DBCO, product number QBD-11223, combines a thiol-reactive bromoacetyl group with dibenzylcyclooctyne (DBCO, also known as DIBAC), a copper-free click chemistry reactive group. The two reactive groups link via a medium-length (40 atoms, 46.1 Å), flexible, single molecular weight, discrete polyethylene glycol (dPEG®) linker. The bromoacetyl group reacts chemoselectively with thiols at pH ≥ 8.0. This differs from the maleimide group, which reacts chemoselectively with sulfhydryls within the range of pH 6.5 – 7.5. The DBCO moiety is a strained cyclooctyne ring flanked by two benzyl rings on either side. DBCO was designed for strain promoted azide-alkyne cycloaddition (SPAAC), also known as copper-free click chemistry.

Specifications

Unit Size	25 mg, 100 mg, 500 mg
Molecular Weight	996.974; single compound
Chemical formula	C₄₇H₇₀BrN₃O₁₅
CAS	N/A
Purity	> 98%
Spacers	dPEG® Spacer is 40 atoms and 46.1 Å
Shipping	Ambient
Typical solubility properties (for additional information contact Customer Support)	Methylene Chloride, Methanol, Acetonitrile, DMF, DMAC, or DMSO.
Storage and handling	-20°C; Always let come to room temperature before opening; be careful to limit exposure to moisture and restore under an inert atmosphere; stock solutions can be prepared with dry solvent and kept for several days (freeze when not in use). dPEG® pegylation compounds are generally hygroscopic and should be treated as such. This will be less noticeable with liquids, but the solids will become tacky and difficult to manipulate, if care is not taken to minimize air exposure.

Documents

References

The post Bromoacetamido-dPEG®₁₂-amido-DBCO appeared first on VectorLabs.

Bromoacetamido-dPEG®₄-amido-DBCO

Vector Laboratories R&D — Sat, 24 Feb 2024 02:15:22 +0000

Description
Specifications
Documents
References

Description

Bromoacetamido-dPEG®4-amido-DBCO, product number QBD-11221, combines a thiol-reactive bromoacetyl group with dibenzylcyclooctyne (DBCO, also known as DIBAC), a copper-free click chemistry reactive group. The two reactive groups link via a short (16 atoms, 17.9 Å), flexible, single molecular weight, discrete polyethylene glycol (dPEG®) linker. The bromoacetyl group reacts chemoselectively with thiols at pH ≥ 8.0. This differs from the maleimide group, which reacts chemoselectively with sulfhydryls within the range of pH 6.5 – 7.5. The DBCO moiety is a strained cyclooctyne ring flanked by two benzyl rings on either side. DBCO was designed for strain promoted azide-alkyne cycloaddition (SPAAC), also known as copper-free click chemistry.

Specifications

Unit Size	25 mg, 100 mg, 500 mg
Molecular Weight	644.55; single compound
Chemical formula	C₃₁H₃₈BrN₃O₇
CAS	N/A
Purity	> 98%
Spacers	dPEG® Spacer is 16 atoms and 17.9 Å
Shipping	Ambient
Typical solubility properties (for additional information contact Customer Support)	Methylene Chloride, Methanol, Acetonitrile, DMF, DMAC, or DMSO.
Storage and handling	-20°C; Always let come to room temperature before opening; be careful to limit exposure to moisture and restore under an inert atmosphere; stock solutions can be prepared with dry solvent and kept for several days (freeze when not in use). dPEG® pegylation compounds are generally hygroscopic and should be treated as such. This will be less noticeable with liquids, but the solids will become tacky and difficult to manipulate, if care is not taken to minimize air exposure.

Documents

References

The post Bromoacetamido-dPEG®₄-amido-DBCO appeared first on VectorLabs.

DBCO-PEG4-Gly-Gly-Gly

Vector Laboratories R&D — Tue, 19 Sep 2023 20:14:31 +0000

Description
Specifications
Documents
Selected References

Description

Water-soluble, substrate for sortase mediated labeling of proteins. Sortase catalyzes a transpeptidase reaction between a specific internal sequence of a protein and an amine group present on the N-terminus of triglycine recently has become an area of great interest. This method of labeling proteins has been denoted as “Sortagging”.

Proteins conjugated to DBCO-Gly-Gly-Gly can be further modified with azide-containing molecules creating site-specific protein conjugates. Examples of creating protein conjugates using sortagging include site-specifically PEGylating proteins,¹ site-specific protein-lipid conjugates,² and constructing peptides and glycosylphosphatidylinositol chimeras.³ Sortase has also been used in peptide synthesis to cyclize peptides to create macrocyclic peptides, glycopeptides⁴ and protein−protein conjugates.

Specifications

Unit Size	10 mg, 25 mg, 100 mg
Molecular weight	845.92
Chemical composition	C38H51N7O13S
CAS	N/A
Solubility	Water, DMSO, DMF
Purity	>95% (HPLC)
Appearance	Grey amorphous solid
Storage Conditions	-20°C. Desiccate
Shipping Conditions	Frozen

Documents

Selected References

Dougan, S. K., et al. (2011). Sortase-catalyzed transformations that improve the properties of cytokines. Proc Natl Acad Sci U S A, 108 (8), 3169-74. [PubMed]
Miller, G. M., et al. (2008). Lipid modification of proteins through sortase-catalyzed transpeptidation. J Am Chem Soc., 130 (48), 16338-43. [PubMed]
Swarts, B. M., et al. (2009). Sortase-catalyzed peptide-glycosylphosphatidylinositol analogue ligation. J Am Chem Soc., 131 (29), 9878-9. [PubMed]
Wu, Z., et al. (2011). Sortase A-catalyzed peptide cyclization for the synthesis of macrocyclic peptides and glycopeptides . Chem Commun (Camb)., 47 (32), 9218-20. [PubMed]
Dougan, S. K., et al. (2012). Preparation of unnatural N-to-N and C-to-C protein fusions. Proc Natl Acad Sci U S A, 109 (30), 11993-8. [PubMed]

The post DBCO-PEG4-Gly-Gly-Gly appeared first on VectorLabs.

DBCO-Gly-Gly-Gly

Vector Laboratories R&D — Tue, 19 Sep 2023 20:14:29 +0000

Description
Specifications
Documents
Selected References

Description

Specifications

Unit Size	10 mg, 25 mg, 100 mg
Molecular weight	598.63
Chemical composition	C274H30N6O8S
CAS	N/A
Solubility	Water, DMSO, DMF
Purity	>90% (HPLC)
Appearance	Yellow solid
Storage Conditions	-20°C. Desiccate
Shipping Conditions	Frozen

Documents

Selected References

Dougan, S. K., et al. (2011). Sortase-catalyzed transformations that improve the properties of cytokines. Proc Natl Acad Sci U S A, 108 (8), 3169-74. [PubMed]
Miller, G. M., et al. (2008). Lipid modification of proteins through sortase-catalyzed transpeptidation. J Am Chem Soc., 130 (48), 16338-43. [PubMed]
Swarts, B. M., et al. (2009). Sortase-catalyzed peptide-glycosylphosphatidylinositol analogue ligation. J Am Chem Soc., 131 (29), 9878-9. [PubMed]
Wu, Z., et al. (2011). Sortase A-catalyzed peptide cyclization for the synthesis of macrocyclic peptides and glycopeptides . Chem Commun (Camb)., 47 (32), 9218-20. [PubMed]
Dougan, S. K., et al. (2012). Preparation of unnatural N-to-N and C-to-C protein fusions. Proc Natl Acad Sci U S A, 109 (30), 11993-8. [PubMed]

The post DBCO-Gly-Gly-Gly appeared first on VectorLabs.

Sulfo DBCO-PEG4-TFP Ester

Vector Laboratories R&D — Tue, 19 Sep 2023 20:14:20 +0000

Description
Specifications
Documents

Description

Sulfo DBCO-PEG4-TFP Ester is a water-soluble, amine-reactive reagent that enables simple and efficient incorporation of DBCO moiety onto proteins, peptides or other amine-containing molecules. The hydrophilic sulfonated spacer arm greatly improves water solubility of DBCO derivatized molecules, in many cases making it completely soluble in aqueous media. The hydrophilic PEG spacer arm improves labeling efficiency and provides a long and flexible connection.

Specifications

Unit Size	10 mg, 25 mg, 100 mg, 500 mg
Molecular weight	851.82
Chemical composition	C39H41F4N3O12S
CAS	N/A
Solubility	Water, DMSO, DMF
Purity	>95% (HPLC)
Appearance	Grey amorphous solid
Storage Conditions	-20°C. Desiccate
Shipping Conditions	Frozen

Documents

The post Sulfo DBCO-PEG4-TFP Ester appeared first on VectorLabs.

ThioLinker-DBCO

Vector Laboratories R&D — Tue, 19 Sep 2023 20:04:45 +0000

Description
Specifications
Documents
Selected References

Description

ThioLinker-DBCO is a water-soluble bis-alkylating labeling reagent that enables site-specific incorporation of DBCO moiety onto antibodies to form well-defined conjugates. This approach involves two steps: (1) disulfide reduction to release the two cysteine thiols and (2) re-forming the disulfide by bis-alkylation via a three-carbon bridge to which DBCO moiety is covalently attached. During this process, irreversible denaturation of the protein, disrupting either their tertiary structure or their biological activity does not occur.

The covalent, site-specific conjugation of PEG to a polyhistidine tag (His-tag) on a protein with bis-alkylating reagents was also reported in literature (see Selected References section).

Specifications

Unit Size	10 mg, 25 mg, 100 mg
Molecular weight	1140.39
Chemical composition	C59H69N3O14S3
CAS	N/A
Solubility	Water, DMSO, DMF DCM, THF, Chloroform
Purity	>95% (HPLC)
Appearance	White to grey amorphous solid
Storage Conditions	-20°C. Desiccate
Shipping Conditions	Ambient temperature

Documents

Selected References

1. Khalili, H., et al. (2012). Comparative Binding of Disulfide-Bridged PEG-Fabs. Bioconjug. Chem., 23(11), 2262-77. [PubMed]
2. Badescu, G., et al. (2014). Bridging Disulfides for Stable and Defined Antibody Drug Conjugates. Bioconjug. Chem., 25(6), 1124-36. [PubMed]
3. Brocchini, S., et al. (2008). Disulfide bridge based PEGylation of proteins. Adv Drug Deliv Rev., 60, 3-12. [PubMed]
4. Balan, S., et al. (2007). Site-Specific PEGylation of Protein Disulfide Bonds Using a Three-Carbon Bridge. Bioconjugate Chem.,, 18, 61-76. [PubMed]
5. Wang, T., et al. (2014). Bis-sulfide bioconjugates for glutathione triggered tumor responsive drug release. ChemComm.,, 50, 1116-1118. [PubMed]
6. Wilbur, T., et al. (1994). Monoclonal antibody Fab’ fragment cross-linking using equilibrium transfer alkylation reagents. A strategy for site-specific conjugation of diagnostic and therapeutic agents with F(ab’)2 fragments. Bioconjugate Chem.,, 5, 220-235. [PubMed]

Site specific conjugation to a polyhistidine tag (His-tag).

Cong, Y., et al. (2012). Site-Specific PEGylation at Histidine Tags. Bioconjugate Chem.,, 23, 148-263. [PubMed]

The post ThioLinker-DBCO appeared first on VectorLabs.

DBCO-NHS Ester, ≥98%

Vector Laboratories R&D — Tue, 19 Sep 2023 19:54:08 +0000

Description
Specifications
Documents

Description

We manufacture our Molecular Biology Grade reagent to ensure the highest possible overall product integrity, consistency and performance for the intended research applications. We offer the highest purity DBCO-NHS Ester available. DBCO-NHS Ester also known as ADIBO-NHS Ester or DIBAC-NHS Ester, is an amine-reactive building block used for modification of amine-containing molecule in organic media. It reacts with primary amines (e.g., side chain of lysine residues or aminosilane-coated surfaces) at neutral or slightly basic pH to form covalent bonds. Short spacer arm adds minimal mass to modified molecules (228.3 daltons).

This product is not recommended for labeling of proteins or any other biopolymers in aqueous buffers due to poor aqueous solubility.

Specifications

Unit Size	25 mg, 100 mg, 1000 mg, 5 g
Molecular weight	402.40
Chemical composition	C23H18N2O5
CAS	1353016-71-3
Solubility	DMSO, DMF, DCM, THF, Chloroform
Purity	≥98% (HPLC)
Appearance	White to slightly grey crystalline
Storage Conditions	-20°C. Desiccate
Shipping Conditions	Frozen

Documents

The post DBCO-NHS Ester, ≥98% appeared first on VectorLabs.

DBCO-PEG4-OH

Vector Laboratories R&D — Tue, 19 Sep 2023 17:26:29 +0000

Description
Specifications
Documents

Description

A bifunctional reagent that contain an azide-reactive DBCO moiety and a terminal primary hydroxyl (–OH) that reacts with a variety of functional groups. A hydrophilic PEG spacer arm provides greater solubility compared to reagents having only hydrocarbon spacers.

Specifications

Unit Size	25mg, 100mg, 500mg
Molecular weight	508.61
Chemical composition	C29H36N2O6
CAS	1416711-60-8
Solubility	DMSO, DMF, DCM, THF, Chloroform
Purity	>95% (HPLC)
Appearance	White to slightly grey crystalline
Storage Conditions	-20°C. Desiccate
Shipping Conditions	Frozen

Documents

The post DBCO-PEG4-OH appeared first on VectorLabs.